Covalent polyester-biomolecule conjugates: advances in their synthesis and applications in biomedicine and nanotechnology

Abstract

Among the variety of polymeric biomaterials, polyesters have a significant position, for example due to their biocompatibility and (tunable) biodegradability. In addition to their established and 'pristine' use as, for example, implants or sutures, the introduction of specific functional biomolecules to polyesters has been attracting increasing attention within the past few years to afford polyester-based functional bioconjugates, which require certain synthesis strategies. Selected recent concepts for these covalent conjugations are summarized in this article in terms of the attachment of biological macromolecules as well as small bioactive drugs on polyesters.

Block Copolymers of Macrolactones/Small Lactones by a “Catalyst-Switch” Organocatalytic Strategy. Thermal Properties and Phase Behavior

“…We recently reported a fast and living organocatalytic ROP of PDL and ω-hexadecalactone (HDL) to high conversion catalyzed by a phosphazene superbase (PSB) 1-tert-butyl-4,4,4-tris(dimethylamino)-2,2-bis[tris(dimethylamino)phosphoranylidenamino]-2λ 5 ,4λ 5 -catenadi(phosphazene) (t-BuP 4 , pK a,ACN = 42.7). 21 The ROP proceeds to high conversion under a wide range of conditions.…”

“…Aliphatic polyesters are important materials with a wide range of properties and applications. − In particular, aliphatic polyesters derived from lactones have tunable mechanical and thermal properties, crystallinity, and are biocompatible/biodegradable materials. , Lactones can be prepared from cheap and renewable bio-based materials such as fatty acids. , In addition, the current development of synthetic methodologies allows the synthesis of new copolymers of lactones with lactides, cyclic carbonates, and epoxides to afford novel biocompatible/biodegradable polymeric materials with diverse properties …”

Novel pranoprofen‐poly(ε‐caprolactone) conjugates: microwave‐assisted synthesis and structural characterization

“…fewer side effects, ease of administration and greater therapeutic effectiveness. 14,15 Various polymer-drug conjugates with NSAID have been described in the literature, and several polymers, such as poly(anhydride-esters), dendrimers, dextran and copolymers of 2-hydroxyethyl methacrylate, were utilized as carriers. [16][17][18][19] Conjugates of NSAIDs with polymers are synthesized to obtain new forms of drugs, which could improve biodistribution, increase solubility, reduce toxicity and extend the duration of drug release.…”

“…Furthermore, the purpose of covalently linking chemotherapeutic agents to specific polymers brought about the fast development of the polymer–drug conjugates field, which, avoiding the rapid release of the drug during in vivo circulation, has shown several advantages with respect to unlinked drugs, e.g. fewer side effects, ease of administration and greater therapeutic effectiveness 14,15 …”

Synthetic Approaches to Combine the Versatility of the Thiol Chemistry with the Degradability of Aliphatic Polyesters

“…[5][6][7] Indeed, for applications in the biomedical field, such as tissue engineering and drug delivery, a functional group could provide an anchoring site for biologically active ligands, thus improving cell adhesion and function, or allow the preparation of degradable particles and polymeric networks with controlled dimension and function. [8] Therefore, methods to integrate amino, carboxyl, hydroxyl, allyl and many other functionalities onto aliphatic polyester chains for fine-tuning of their physical and biological properties have been sought, and review papers are available in the literature. [2,[9][10][11] However, because of the reactivity of the polyester backbone, which can undergo hydrolytic degradation with a consequent drop in the molecular weight and change of the physical properties of the material, the controlled introduction of functional moieties requires some synthetic effort.…”